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Synthesis of a Pseudo Tetrasaccharide Mimic of Ganglioside GM1
Author(s) -
Bernardi Anna,
Boschin Giovanna,
Checchia Anna,
Lattanzio Maria,
Manzoni Leonardo,
Potenza Donatella,
Scolastico Carlo
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199906)1999:6<1311::aid-ejoc1311>3.0.co;2-w
Subject(s) - chemistry , tetrasaccharide , ganglioside , glycosylation , stereochemistry , total synthesis , dihydroxylation , cholera toxin , glycosphingolipid , enantioselective synthesis , sialic acid , biochemistry , catalysis , polysaccharide , microbiology and biotechnology , biology
The pseudo tetrasaccharide 2 was designed to mimic ganglioside GM1, the membrane receptor of both the cholera toxin and of the heat‐labile toxin of E. coli . Compound 2 retains the Gal and Neu5Ac recognition determinant of GM1 and uses as the scaffold element a new, conformationally restricted cyclohexanediol (DCCHD 3 ), with the same relative and absolute configuration of natural galactose. The diol 3 was enantioselectively synthesized by an asymmetric Diels–Alder reaction, followed by dihydroxylation of the resulting cyclohexene. Glycosylation of 3 with the sialyl donor 17 and the Galβ(1‐3)GalNAc donor 15 , followed by removal of the protecting groups, completed the synthesis of 2 .